Azo dyestuffs insoluble in water and process of making them.



AUGUST LEOPOLD LASKA AND ARTHUR ZITSGHER, OF OFFENBACI-I-ON-THE-MAIN, GER- MANY, ASSIGNORS TO CHEMISCHE FABRIK GRIESHEIM-ELEKTRON, 0F FRANKFORT- ON-THE-MAIN, GERMANY, A CORPORATION.

AZO DYESTUFFS INSOLUBLE IN WATER AND PROCESS OF MAKING THEM.

No Drawing.

ble in Water and Processes of Making- Them, of which the following is 'a"specification.

Our invention relates to the production of azo dyestuffs insoluble in water and of a remarkable fastness and consists in combining a diazo compound not containing a sulfonicor carboxylic-group with an acidyl-2- amino 3 naphthol. As diazo compounds can be used those derived from anilin, its homologues and substitution products, such as from orthoand para-anisidin, also from chloro and nitro derivatives, from chloroand nitroanilins, chloroand nitrotoluidins,

chloroand nitroanisidins, from alphaandbetanaphthylamins, from amino azo compounds, the tetrazo compounds of diamino bases, such as benzidin, tolidin, dianisidin, diaminodiphenylurea, and others.

Azo dyestufi's derived from 2-acidylamino- 3-naphthols have not hitherto been known. Compared with the insoluble dyestuffs, describedby Vitt in fBerz'chze der deutsohen chemise/ten Gesellschaft 'vol. 29, page 2919, and in the German- Letters Patent No. 93312, derived from acidyl-l-aminot-naphthols the present dyestuffs are distinguished by their essentially greater fastness to chlorin.

The dyestufl's having probably the for- Specification of Letters Patent.

Patented July 6, 1915.

Application filed June 16, 1914. Serial No. 845,335.

that the cotton goods, which are impregnated with the alkaline solution of an acidyl-2-amino-8-naphthol, are developed with a diazo compound without previously drying, especially stronger shades are obtained than with the well known dyestuffs derived from acidyl 1 amino 4 naphthol. The combination can be effected in an acid, neutral or alkaline solution according to the kind of diazo compound.

The following examples illustrate the in vention, the parts being by weight:

Emample 1.

A diazo solution, prepared in the usual manner from 16.8 parts of nitroanisidin 4.1.2. (OCH NH NO,::1 2 4) is poured while well stirring into an aqueous suspension of 27 parts of benzoyl-2-amino-3-naphthol,'prepared by dissolving the latter in diluted caustic soda lye and precipitating with diluted acetic acid. The dyestuff separates in red flakes, it is filtered, when the combination is complete, washed until neutral and preferably used in theform of a paste. \Vhen dry it is a brillant red powder and yields, when converted into lakes, red pigment colors of an excellent fastness to oi Production of the olg estufi on the fiber.- The goods are impregnated with the following solution: 12 grams of benzoyl-2-amino 3-naphthol, 20 com. of caustic soda-lye 3i B., 25 grams of ricinoleate of soda are mixed to a paste and dissolved in 500 com. of boiling water, and the whole is made up to 1 liter.

The well dried goods are printed with a mixture of: 500 com. of the diazo solution, 500 grams of tragacanth-thickening 1 20,25 com. of a solution of sodium acetate 1: 1.

For preparing the diazo solution 16.8 grams of nitro-anisdin 4.1.2 (OcH zNH z NO :1:2:4) are diazotized in the usual manner, to the solution 12.5 gr. of aluminium sulfate are added and the whole is made up to 500 com. After printing the goods are dried, washed and soaped at 5070. In this manner deep red prints are obtained.

By producing the dyestufi on cotton-yarn according to the process described in the specification of the application Serial N0. 7 95456, a brilliant red of an excellent fastness is obtained.

Ewamplc 92.

The bleached or raw cotton-yarn, previously well boiled with carbonate of soda or caustic soda, isimpregnated at about 10 C, with a solution of benzoyl-Qfi-am monaphthol as described in, Example 1, well a wrung out and having cooled dyed in a dye-V bath of the following constitution: 300 com. of the diazo solution are mixed with 42 com. of a solution of cupric chlorid 40 12 com. of a solution of chromic acid 1:10 and 110 com. of aluminium sulfate 12 B. and shortly before dyeing (l'ccm. of a solution of sodiuni acetate 1:1 areadded. The whole is made up to 1 liter.

D6020 s0Zut-z'0n.2-1 grams of dianisidinbase are dissolved in 21 com. of hydrochloric acid of 20 Be. and 250 com. of boiling water; to the cooled solution are added 200 grams of ice and com. of hydrochloric acid of B. and then 16 grams of sodium nitrite dissolved in 50 grams of water are allowed to run in while well stirring. The whole is made up to 1 liter. After dyeing the yarn is well wrung out, well washed and soaped at 70-80 C. In this manner beautiful reddish blue tints are obtained;

lnstead of Q-benzoylamino 3-naphthol its s ibstitution products, such as Q-halogenbenzoylamino 3 naphthol or 2-nitro-benzoyl amino-5-naphthol, or other acidyl derivatives of 2.3-amino-naphthol can be-used, such as :2-acetylamino-3-naphthol, 3.3 -dioXy-22 -dinaphtylurea and so on.

-B., V wherein R means an aromatic'radical and n a number, less than 3, which dyecombining a diazo compound not contain-' ing a sulfonicor carboxylic-group with an ac1dyl-2am1no-3-naphthol, which dyestuffs have probably the formula stuffs are adapted to yield when converted into lakes pigment colors of an excellent fastness to oil.

2. Process of making azo dyestuifs', insoluble in water, consisting in combining a diazo compound not containing a sulfonicor carboXylic-group with an acidyl-Q-amino- 3-naphthol. i

3. Process of making azo dyestuffs, insoluble in water, consisting in combining a diazo compound notcontaining a sulfonicor carboxylicgroup with an acidyl-Q-amino- 3-naphtl1ol on the fiber. That 7Q: claim the foregoing as .our invention, we have signed our names in presence of two witnesses, this fourth day of June, 1914?. 7

AUGUST LEOPOLD LASKA. ARTHUR ZITSCHER.

\Vitnesses HEIQIANN \VEIL,

FRIEDRICH QUEHL. 

